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Top 20 Fashion Icons—From Marilyn to Madonna and More!

by
Tiffany Tse

From Grace Kelly’s refined aesthetic to Madonna’s rebellious sensibilities, these icons leave us with an unforgettable sartorial legacy, inspiring women then and now to replicate their look. Click through our slideshow to see who made the cut.

Marilyn Monroe

Monroe’s Hollywood image was that of sultry bombshell, a reputation she fostered by wearing skintight dresses and va-va-voom tops that flaunted her figure to perfection.

Jean Seberg

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Hulton Archive/Getty Images

Although Seberg was actually from small-town Iowa, the actress’s penchant for Breton stripe T-shirts, crisp blouses, and slim trousers came to personify everything cool and sophisticated about Parisian style.

Jacqueline Kennedy Onassis

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Paul Popper/Popperfoto/Getty Images

The former first lady was the picture of classic, all-American polish. Even after she remarried to Greek tycoon Aristotle Onassis, shifting her style from pillbox hats and shift dresses to oversize sunglasses and head scarves, the public continued to remain fascinated by her look.

Twiggy

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Popperfoto/Getty Images

The British model’s gamine look—lanky limbs, a pixie crop, and doll-like eyes, not to mention the Mary Quant minis and mod dresses she often wore—made her a poster child of the ’60s.

Jane Birkin

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GAB Archive/Redferns

Hermès’s renowned Birkin bag is named after the British actress, who captured a free-spirited, bohemian-inspired style in the ’60s—think slightly sheer blouses, micro shorts, and flared jeans—that felt decidedly French.

Diana Ross

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Michael Ochs Archives/Getty Images

The word “fierce” is part of Beyoncé vernacular now, but back in the ’60s, it belonged solely to Ross. The Supremes singer’s name is synonymous with glitz and glamour, thanks to her bedazzled outfits, bigger-is-better jewels, and voluminous coif.

Faye Dunaway

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Hulton Archive/Getty Images

We can’t think about Dunaway without envisioning the actress’s signature beret hats, short-sleeve sweaters, and midi skirts, the elegantly appealing look she sported in 1967’s Bonnie and Clyde and also off the clock.

Bianca Jagger

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Ron Galella/WireImage

Often spotted in turbans, sequined pieces, and truly fabulous hats, Jagger was fashion-forward even for her time. The model—and Studio 54 fixture—embraced the bold, flashy outfits that cemented her fashion icon status.

Anita Pallenberg

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Dove/Express/Getty Images

For the paramour of more than one member of the Rolling Stones in the swinging ’60s, it’s only fitting that Pallenberg commandeered a rock ’n’ roll sense of style: swingy mini dresses, wide-brimmed hats, fringed vests, and kohl-rimmed eyes.

Lauren Hutton

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Ron Galella/WireImage

Hutton’s approach to dressing is best described as effortlessly natural, much like the gap-toothed smile that became her beloved trademark. The actress and supermodel wore button-downs, slouchy pants, and simple T-shirts with an enviable laissez-faire attitude.

Diane Keaton

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Getty Images

Who could forget Keaton dressed in a vest, tie, and bowler hat in her famous role as Annie Hall? The actress’s borrowed-from-the-boys style revolutionized the way women dressed in the late ’70s and early ’80s—and we’re thankful for it!

Debbie Harry

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Michael Ochs Archives/Getty Images

As the frontwoman of Blondie, Harry is punk royalty, and her wardrobe reflected that with DIY-inspired, shredded rocker T-shirts, black jeans, and tough biker jackets galore!

Madonna

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David Mcgough/DMI/Time Life Pictures/Getty Images

Madonna has continued to reinvent her look over the decades, but it’s the Material Girl’s first appearance on the scene—wearing conical bras and studded bustiers in the ’80s—that make her a fashion trailblazer.